3-氨基苯甲酰胺 → 3-[2-(4-Iodo-phenoxy)acetyl-amino]-benzamide

HRID 1945389

反应方程式

HRID 1945389 反应方程式
[I:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH2:19])=[O:18].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH2:19])=[O:18])=[O:10])=[CH:11][CH:12]=1

参与物

7

反应物 5

HCID 16453-氨基苯甲酰胺HCID 74658对碘苯氧乙酸HCID 757711-羟基苯并三唑(HOBT)HCID 81531N,N-二异丙基乙胺HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐

产物 1

HCID 248112093-[2-(4-Iodo-phenoxy)acetyl-amino]-benzamide收率 88.4%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

To (4-iodo-phenoxy)acetic acid (83.5 mg, 0.3 mmol), 3-amino-benzamide (61.3 mg, 0.45 mmol), N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (86.3 mg, 0.45 mmol) and 1-hydroxybenzotriazole (HOBt) (61.3 mg, 0.45 mmol) in DMF (3 ml) was added N,N-diisopropylethylamine, redistilled (DIPEA) (0.08 ml, 0.45 mmol). The mire was stirred overnight, and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2CH2:MeOH=6:1) to give 3-[2-(4-iodo-phenoxy)acetyl-amino]-benzamide as a white solid (105.1 mg, 88.4% yield).

后处理

  1. distillationredistilled (DIPEA) (0.08 ml, 0.45 mmol)
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (CH2CH2:MeOH=6:1)

来源与证据

ORD记录
ord-22e1170d8cfd4a6c8825cfbc2ed79f3b
来源数据集
uspto-grants-2013_03
专利号
US08394799B2

关联笔记

加载中…